text: A monosubstituted cyclohexane is one in which there is one non-hydrogen substituent in the cyclohexane ring. The most energetically favorable conformation for a monosubstituted cyclohexane is the chair conformation with the non-hydrogen substituent in the equatorial position because it prevents high steric strain from 1,3 diaxial interactions. In methylcyclohexane the two chair conformers are not isoenergetic. The methyl group prefers the equatorial orientation. The preference of a substituent towards the equatorial conformation is measured in terms of its A value, which is the Gibbs free energy difference between the two chair conformations. A positive A value indicates preference towards the equatorial position. The magnitude of the A values ranges from nearly zero for very small substituents such as deuterium, to about 5 kcal/mol (21 kJ/mol) for very bulky substituents such as the tert-butyl group. Thus, the magnitude of the A value will also correspond to the preference for the equatorial position. Though an equatorial substituent has no 1,3 diaxial interaction that causes steric strain, it has a Gauche interaction in which an equatorial substituent repels the electron density from a neighboring equatorial substituent.